Cyanoacetamide → HCID 12968695, compound

HRID 1017698Notes

Reaction equation

HRID 1017698 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=O.[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17].C[O-].[Na+].[H-].[Na+]>CN(C)C=O.C(O)(=O)C.O.CO>[C:16]([C:18]1[C:19](=[O:20])[NH:21][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])=[CH:4][CH:3]=1)#[N:17]

Participants

9

Reactant 4

HCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 54435623HCID 54435623, compound

Product 1

HCID 12968695HCID 12968695, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3-dimethylamino-1-(2-methoxyphenyl)-2-propene-1-one (5.74 g); cyanoacetamide (2.48 g) and sodium methoxide (from sodium hydride (50%, 4.32 g) and methanol (3.5 ml) in dry dimethylformamide was heated under reflux for 10 hours. The reaction mixture was poured into water, acidified to pH 4 with glacial acetic acid and extracted with ethyl acetate. The ethyl acetate extract was evaporated under reduced pressure to low volume and water was added to cause precipitation of a crude product (3.67 g) which was collected and recrystallized twice from dimethylformamide to yield the title compound, 1.68 g, m.p. 236°-238° C.

Workup

  1. temperatureunder reflux for 10 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. customwas evaporated under reduced pressure to low volume and water
  5. additionwas added
  6. customprecipitation of a crude product (3.67 g) which
  7. customwas collected
  8. customrecrystallized twice from dimethylformamide

Sources & evidence

ORD record
ord-cb81c79b29974afe92ed4e89d2e29549
Source dataset
uspto-grants-2002_11
Patent number
US06479520B1

Reaction notes

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